During the first two days of kindergarten, a girl sobs. On day three, she dials it down to sniffling and decides to join four other students at the clay table. Her teacher overhears this conversation:

Boy: Why are you crying?

Girl: Because I miss my Mommy.

Boy: We all miss our mommies.

This normalizing of emotion through the provision of context has an apparently good effect. The girl nods, albeit with a look of resignation. The next morning, for the first time, she hugs her mom and says goodbye without protest.

The boy, our separation guru, grasps an essential truth. Growing-up is hard, but also necessary and unavoidable, so we might as well accept it and get down to the business of making snakes out of clay. T’was ever thus and always thus will be… except, of course, that times change, and leave-taking these days takes on greater complexity and nuance — which means that independent schools face new challenges in helping children make a smooth separation from their home and their parents.

The New Kindergartener

I love the Gesell Institute series of classic child development books — Your One-Year-Old, Your Two-Year-Old, and on up — for two reasons. First, they are so wise and eloquent. Second, they provide an enlightening window on the past.

For example, Your Five-Year-Old, originally published in 1979, asks the following question of the reader who wishes to know if a young child is on track in terms of independence and school readiness: “Can he travel alone in the neighborhood (two blocks) to a store, school, playground, or the homes of friends?”

In Your Six-Year-Old, the authors ask: “Can he travel alone… four to eight blocks?” It’s hard to imagine many parents allowing this today.

Times have changed. Polly Klass, Elizabeth Smart, Jaycee Dugard: every parent knows these names and the chilling stories attached to them. In the past, noncelebrity news stayed local, but today we have a 24-hour news cycle hungry for product-selling attention. This leads to a fear industry that exaggerates everyday risks and sensationalizes highly dramatic but low-probability occurrences like abduction. Jittery parents justify keeping a close eye and tight hold on their children, saying, “I could never live with myself if (fill in the blank).” The rule is, “Better safe than sorry.”

This level of caution and surveillance leaves the average five- or six-year-old protected, but hesitant and inexperienced in unfamiliar environments. Few have had the chance to travel alone anywhere, certainly not to the store or the playground. Few have the opportunity to get even a dash of street smarts: to practice getting themselves out of even a minor jam, to develop wayfinding skills, to navigate their neighborhood and choreograph their day — all valuable components of school readiness.

Experienced kindergarten teachers see the fallout from this increasingly supervised life — with many incoming kindergarteners more sophisticated than past cohorts, but also clingier and less sure of themselves. Some have visited Paris or Hawaii, but haven’t developed the skill to fall asleep on their own. They may know how to operate an iPhone, but are reluctant to spend time alone in their room, go on a play date or sleepover, or be dropped off at a birthday party without an adult companion (parent or babysitter) in tow.

Some dash right into the crowd the first day of school, but get unsettled when they discover that teachers don’t offer them the kinds of choices and accommodations that are automatically provided at home.

A special challenge for students in independent schools is the geographic diversity of the students. A child’s neighborhood is full of familiar faces, the local public elementary school a familiar landmark. Even if the rising kindergartner hasn’t been inside the school, she’s passed it often. But because independent schools are selected by families and because they draw from many preschools in a broad geographical area, families may have a long commute and the incoming student might know few, or no, children in her class.

In addition, flexible birthday cut-offs and redshirting (the protective strategy of holding children back a year to help the less mature, typically boys, cope with an accelerated academic curriculum) mean that kindergarten classes have broader age spans than in the past, often a full year-and-half or more.

Despite independent schools’ cozy class sizes, devoted and well prepared teachers, and attunement to the best practices for separation, this distance from home and range of age and maturity (and immaturity) of fellow students can add to a student’s sense of uncertainty.

The New Kindergarten Parent

Neighbors to the two small boys who moved onto the street: Where do you go to church?

Children: We don’t go to church, we go to Country Day.

One school head contrasted his experience in his first year at the helm of an independent school with his struggle to find creative ways to engage parents in the low-income area where he had previously worked. “At my old school,” he said, “we had nearly empty classrooms at back-to-school night. At this school, the parents are furious if you say you’ve reached the limit of chaperones for the fieldtrip. Some days I can’t get them out of my office with a gun.”

I once gave a talk to a misty-eyed group of 40 parents of graduating sixth graders — whose children were moving on to more than a dozen different middle schools. I called it “Cast Out of Eden.” The subject was respecting normal parental nostalgia and even grief about leaving the lower school community.

Psychologist Michael Thompson, who writes eloquently about parent/school relationships, notes that past generations of independent school parents dropped off their children at kindergarten and picked them up at 12th grade graduation with little more than a wave in between. In The Blessing of a Skinned Knee, I talked about a starchy British father who would only attend a school play if one of his children had seven lines or more. But today’s independent school parent finds school a warm and welcoming haven in an increasingly competitive and isolating world. This makes a school so alluring — and so hard to leave. The effect can cause parents to send unconscious clues to their children that it’s best if mom or dad sticks around a bit longer, especially during the early days.

And then there’s the kindergarten classroom itself: so colorful, warm, and inviting. A rug for circle time! Hmm… New friends for Trevor! New friends for me? Certainly many parents are delighted by the new freedom afforded them by having a child in big-kid school, but, for others, it’s difficult to turn away, to let go.

The verb “parenting” was not part of the lexicon of past generations, and few parents tended to the art and science of parenting beyond reading Spock and consulting with relatives or the pediatrician when they hit a rough patch. In contrast, today’s parents are ambitious and determined to do it right and produce children who reflect their talent and devotion. Parents magazine and The Today Show recently surveyed 26,000 women about their biggest, darkest secret. The secret turned out to be… judgment. The women respondents confessed that they harshly judged both other mothers and themselves.

And what is the first week of kindergarten if not Judgment Day? Parents study the evidence: Did my child cry the loudest? Will I have to stay the longest? Will I be the only one whose daughter doesn’t look back once? Are all my parenting flaws showing already?

How Schools Can Guide Parents in the Art of Separation

Perhaps the best advice I can give schools and parents comes from T. S. Eliot. In his poem “Ash Wednesday,” he writes, “Teach us to care and not to care/Teach us to sit still.”

Let’s deconstruct this dictum a bit.

Separation practices that are ruthlessly matter-of-fact — the just-pry-’em-away-from-their-parents-in-the-parking-lot approach — can have the unintended consequences of forcing children to soldier on in order to protect against humiliation. The downside of this approach? Consistently sour morning battles, crabby afternoons, bedtime meltdowns, or outright school refusal.

At the other extreme is what the Buddhists call “idiot compassion,” and 12-step programs call codependency: practices in which we handicap people because we cannot bear their suffering. This happens to both parents and students when separation practices are overly precious, gentle, and drawn-out, when we pamper kids and cater to parents’ desire to hang out as long as possible, stretching out time and resources and depriving everyone of the opportunity to get on with the business of educating the children.

What follows are some strategies schools can use to help parents help their children through the process of separation.

Some prevention strategies

Most systematic programs for socializing puppies require the owner to expose the dog to many different kinds of surfaces underfoot (wet grass, linoleum, sand, gravel, tall weeds); sounds (cars honking, gunshots, loud music, cats meowing, an electric saw); people (the elderly, crying babies, those in hats, with beards, in uniforms), and human environments (crowds, different cars, a dog park, city streets with traffic) so the dog will grow accustomed early to the texture of life and not become fearful, skittish, or aggressive.

At an orientation meeting for incoming parents or in your new family information packet, encourage parents to provide their children with lots of opportunities to practice independence during both the summer before and weeks leading up to the start of school: stay alone with a babysitter, go on a play-date or outing with another child’s family, spend the night at a friend’s or grandparent’s or cousin’s house, ride a bike with other kids in the neighborhood (even just down the block), go to day camp, or simply spend some free-range time alone with other children while visiting relatives or on vacation.

These experiences help build flexibility and ease in new environments.

Expect regression

When the boy who separated beautifully for preschool balks or whines or bawls when left at the kindergarten door, parents naturally think: He used to love school! What happened? Must be something awful! But the gregarious toddler may be passing though — or have landed in — a more tentative, discerning, cautious, slow-to-warm stage. Or the incoming kindergartner, both aware and wary of the changes in his routine, may have transient difficulty falling asleep or some bad dreams or start wetting the bed for a few nights.

This doesn’t mean that his parents have made a terrible mistake, chosen the wrong school, or that the child has developed an anxiety disorder. Kids go through phases. Transitions bump up worrisome behaviors. Schools can help parents anticipate normal regression and prevent overreaction to natural shifts and periods of adjustment by letting parents know what to expect. Here again, even the titles of the Gesell books are an education. The subtitle of Your Five-Year-Old is Sunny and Serene, but of Your Six-Year-Old it’s Loving and Defiant. And while, in six-year-olds, nervous tics and tantrums (I hate you! I hate school!) pop up (in previously easy going five-year-olds), doom-and-gloom worries and fretting often emerge at seven. The subtitle of that volume? Life in a Minor Key.

In other words, childhood is full of phases. It’s when parents confuse a snapshot of their child at any particular moment with the epic movie of his life that panic trumps reason.

Watch the gap

Summer’s more leisurely schedules, vacations, picnics, and family time is followed by an acceleration of activity in the weeks or days leading up to the start of school. Shopping for clothes and school supplies, filling out forms and planning carpools takes up a great deal of the parents’ time. When this bustle of activity culminates with The Big Goodbye in the parking lot or at the classroom door, both parent and child may feel a shock of poignancy or regret. Having an attentive mom or dad or the nanny right there with me! in the classroom can lead the child to want to hold on tight, to reclaim the closeness of a slower season.

Advising parents to end vacations and run errands early, leaving time for relaxed togetherness during the week before the start of school, can help decrease the perception of an abrupt abandonment.

Also urge parents to make the first day as easy-going as possible by working backwards, starting with an unhurried late afternoon, a pleasant suppertime, a relaxed, familiar, same-old bedtime ritual the night before, and a sufficiently early wake-up to allow the new incoming student time to make an outfit change, complain that her tummy feels funny even when presented with her favorite waffle, and to be captivated by a rolly-polly bug on the sidewalk.

The Talk

Encourage parents to elicit and answer questions about school in the week or the day before school starts, not right before bed or en route. And discourage enthusiastic hyperbole. Adults lose credibility fast when they say, “You’re so lucky to be in Ms. Lloyd’s kindergarten class! It’s going to be so fabulous! You’ll just love it! The kids will all be great!”

When parents try to sell or spin joy, by taking on the role of public relations agent for the school and their child’s experience in it, even the most trusting five-year-old will grow suspicious and either tune the parent out or worry that the real truth is being covered up.

Instead, like Winnie the Pooh, the parent can venture out on a gentle little “Explore.” “School starts next week. Anything you’re wondering about? Any questions about how it will be?”

A friend of mine’s son, anxious about going off to college, asked his mother, “How will I get food?” The incoming kindergartner has similar basic questions: “How will I find the bathroom? What will I do if I miss you a lot? What will happen if I throw up?”

Child development specialist Betsy Brown Braun tells parents to explain to children that worry and excitement can feel the same, that excitement doesn’t always feel like happy anticipation, and that worries go away when the unfamiliar becomes familiar. Parents can remind their children that first-day jitters are natural, and that most every child in their class is feeling the same way about now. To a child who seems quiet, irritable, super goofy, or wired-up, a parent can say: “When I started kindergarten, I was nervous, too. And then on the first day of middle school and high school and college and graduate school. It just seemed to go that way for me, and then it always turned out fine.”

If this degree of drawing out and encouragement feels like leading the witness or a bit precious or indulgent, think of it as prep work, preventive mental health, an investment in a smooth transition and good adjustment.

Make arrival and departure time a priority

In my practice, one of the first questions I ask of parents whose children are having difficulty with school adjustment is if the child tends to be dropped off early, in the nick of time, or late. And I ask the same questions about pick-up: Does your child know who will pick her up each day? Is that person ready and waiting when school gets out? Are there any times the schedule got mixed-up and she was left at school? I really probe about this. If the parent says that she (or he, or the carpool driver or the caregiver) is “sometimes late,” I ask for a definition of “sometimes.” How often? I make such a big deal about this because it has such a big impact on kids. Four- and five-year-olds are the transition police. Unable to generate an adult-like range of explanations, they become like Piaget’s seven-month-old research subjects — if you put the ball behind the curtain, they don’t even look for it; it’s gone forever. In other words, they lack object constancy. While waiting for a tardy parent, many children, especially those of a sensitive nature, will resort to catastrophic thinking: My mommy/babysitter is dead. My mommy doesn’t love me anymore. I will never ever see her again.

Tell parents how reassuring it is for children to know who will be picking them up. If families find themselves with a chronically late carpool team member, encourage them to drop out and find an alternative plan — even if the tardy driver is a longtime nanny, a good friend, or the next-door neighbor.

Emphasize the power of consistency and predictability — how knowing the who and when of the boundaries of the school day creates security in children, how a tense and hurried morning and split-second arrival isn’t invigorating, but leads to a tense and awkward re-entry into the rhythm of the classroom. Reinforce this message in every form possible: in written materials, orientation meetings, and — if problems with lateness are cropping up right away — with an email or call home. If it’s a chronic problem with a particular family, make it a top agenda item at the first parent-teacher conference.

Keep the script short at the door

Parents know better than to say (although I’ve heard it): “Sweetie! Are you sad that Mommy is leaving? Do you want to cry?” But it’s common to hear parents punctuate sentences with what the teachers call “The Big Okay.”

“I’m leaving now, okay? Okay? Okay?” until the child wails, “Nooooo!”

Tell parents, instead, to make it quick and efficient. If they wish to take first-day-of-school photos, request that they do so at home rather than in the bustle of the classroom — an environment where the agenda is building the team rather than celebrating each individual star. And saying, “What color pen should I use to sign in with today, honey?” just introduces more options and connection.

A good parting phrase? “Have a great day. I’ll see you at lunch time/this afternoon and you can tell me all about it.” Without getting too adorable or complicated, you might come up with a private goodbye ritual — a special handshake or salute or code word that means, “I love you! You’re my guy.”

After the first day, resist trawling for trouble

Mom: How was your day, sweetie?

Child: Fine.

Mom: (Oh no! What is he hiding from me?)

I treasure the wisdom offered to me by parents and teachers on the book-signing lines after my talks at schools. In Nashville last spring, a woman introduced herself and told me that she was an orthodontist. Her motto for parents? “Don’t ask if the braces hurt.” To this, I add, caution parents against gathering data to reassure themselves.

Don’t ask… if her teacher is nice. It invites a negative assessment of the person you’re trusting to care for your child every day, all year long. Don’t ask who she sat with at lunch, what she ate, or if she used the bathroom. It’s none of your business. Don’t cross-examine. If kids sense that they need to reassure you, it causes them to doubt even perfectly tolerable experiences.

Do ask… what she found most interesting, and link up school learning with home activities when possible. This continuity offers a “we’re all on the same page/one big community” kind of security. If the students are studying bugs and worms, dig up some dirt in the backyard and see what lies beneath. Read The Very Hungry Caterpillar. Be a subject-matter cheerleader rather than a happiness detective.

Of course, if your child spontaneously begins an information download or shares a highlight about the day, you can be rapt. Oh! Wow! Sounds like you had so much fun painting sunsets and monsters with your new friend, Olivia! I’ll bet daddy and grandma will be excited to hear about this.

Let them know you held them in mind but survived and thrived

All therapists see kids who have to come home early from sleep-away camp or college to keep an eye on their parents’ fragile marriage, depression, or drinking. They worry: Will mom and dad be okay? I’d better go check.

Let parents know that even the wee kindergartener benefits from hearing how well they functioned on their own — while, of course, keeping him in mind. To be reassuring, parents might say something like, “Today I noticed that more of the leaves on the maple trees are turning red and gold. It’s going to be so beautiful soon. And I thought of you when I saw a huge banner in front of the museum advertising the new fossil show…. And what did you look at in school today?”

Okay, When to Worry

Unfortunately, for some students, the temporary regression triggered by starting school does not abate. What are the red flags? Any group of these behaviors: a previously toilet-trained child is wetting the bed every night, waking up complaining of nightmares, chewing on his shirt, complaining of lots of stomachaches and headaches, or protesting if parents want to leave him with a babysitter.

Encourage parents who notice these signs of distress to ask the teacher whether or not the child brightens soon after arriving at school or if he is withdrawn, irritable, or provocative with other children. Does he approach new activities with enthusiasm or react to frustration with whining, tears, or tantrums? Some parents want to wait it out, fearing they will prejudice the teacher against the child or get him “labeled” if they tell the school about only problems, but the kindergarten teacher is an experienced surveyor of the range of normal behavior in children this age and her observations and insight can lead to a helpful plan of action.

Put Money in the Bank

The new web-based parent information portals — Pinnacle, SnapGrades, Powerschool — are a mixed bag for schools because the steady flow of information from school provides, in the language of teenagers, “tmi” (too much information). Parents repeatedly scan the screen, hit the refresh button, and get increasingly agitated about what they do, or don’t, see. I saw on Pinnacle that you didn’t hand in your science project today… He took his history test second period! Why isn’t the grade posted yet? Why has his national varsity ranking dropped? In many cases, these services invite overinvolvement, or addiction-like behavior.

Yet, one form of increased school/parent communication yields nothing but positive benefits.

Bob Ditter, a psychologist who gives guidance to summer camp administrators and counselors, recommends that the counselors send a brief email to each family telling parents that the bus trip was happily uneventful and adding one specific and personal detail about their child: I’m already enjoying his sense of humor…. It’s so nice to have her bright smile in our group…. He was so helpful to other kids as they unpacked…. He proudly showed me his blue flippers.

Ditter calls this small gesture “money in the bank.” The investment of time pays off if the counselor has to call a parent about a behavior problem or rule violation later in the summer because there’s already a foundation of mutual respect in the relationship. A short email home after the first day of school demonstrates your appreciation for your new student as both an individual and a member of your team. You can call or write to say, “Lucas had a great day. He told his classmates about your new puppy, Prana, and graciously helped a new friend open his lunch box.” This sets a tone of mutual respect and collegiality.

Seeing the Whole Sky

German poet Ranier Maria Rilke wrote, “Once the realization is accepted that even between the closest human beings infinite distances continue, a wonderful living side by side can grow, if they succeed in loving the distance between them which makes it possible for each to see the other whole against the sky.”

The boy who said: “ We all miss our mommies,” understands. Growing up is work. It’s hard to become a member of a team, to be in a strange new place, to miss your familiars. And the new kindergarten parent — so knowledgeable, devoted, eager, wary of judgment, and aware of loss — has a hard time, too. To both parent and child, I offer consolation and respect for the initial bumps on the path and the happy prospect of a richer and deeper connection as the year progresses and each sees the other more fully. Mom! Mom! Did you know that the sun is actually a star? And that it’s the closest one to earth? And that in China they don’t see a man in the moon; they see a rabbit? And that my friend Jack has a real tarantula for a pet! Did you? Did you?

And to school leaders, I encourage you to be understanding, kindly, firm, and confident in guiding parents and children in their shaky first steps of necessary separation and in their pursuit of loving the distance between them.

Special thanks Lois Levy and Baudelia Taylor at the Center for Early Education (California), Joan Martin at Crossroads School (California), Julie Tepper at The Mirman School (California), Tina Wooten at Stratford Academy (Georgia), and Los Angeles-based child development specialist Betsy Brown Braun for their insights into the art of separation.